proline dl-form → 1-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate

HRID 457919

반응식

HRID 457919 반응식
N1CCC[CH:2]1C(O)=O.[C:9]([O:13][C:14]([N:16]1[CH2:20][C:19](=[N:21][O:22][CH3:23])[CH2:18][C@H:17]1[C:24]([OH:26])=[O:25])=[O:15])([CH3:12])([CH3:11])[CH3:10].CO.C[Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1>[CH3:23][O:22][N:21]=[C:19]1[CH2:20][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:15])[C@H:17]([C:24]([O:26][CH3:2])=[O:25])[CH2:18]1

참가 물질

6

반응물 4

HCID 614proline dl-formHCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

생성물 1

HCID 585854781-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of the oximether- and/or olefin-type 2-pyrrolidinecarboxylic acid intermediate, e.g. (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid (0.648 g, 2.5 mmol), in a 1:1 mixture of methanol and toluene (35 ml) was made. Trimethylsilyl diazomethane (3.8 ml of a 2M solution in hexanes, 7.5 mmol) was then added dropwise to the stirred solution at room temperature under nitrogen. After completion of the evolution of nitrogen gas, the resulting yellow solution was evaporated in vacuo, and the residue filtered through a pad of silica gel, eluting with ethyl acetate. Removal of solvent from the filtrate gave the methylester product, e.g. 1-tert-butyl 2-methyl(2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate, as a yellow oil (0.646 g, 95% yield).

후처리

  1. customAfter completion of the evolution of nitrogen gas, the resulting yellow solution was evaporated in vacuo
  2. filtrationthe residue filtered through a pad of silica gel
  3. washeluting with ethyl acetate
  4. customRemoval of solvent from the filtrate

출처 및 근거

ORD 기록
ord-d1b970716bbc4b3c94fe462585b988e2
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189754B2

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